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In devarim 1:1 rashi comments that the various places listed are in fact veiled references to episodes in which the Jewish people rebelled. Thus Moshe was offering a kind of concealed rebuke. My questions are:

  1. Why is the list of transgressions out of order? The list of rebuke items is not in chronological or any other order that I can ascertain.
  2. Why are items left out? Once he's rebuking them why not point out every time they failed?
  3. Why is he rebuking them when they didn't do it? This is not the generation that worshiped the golden calf or sent the spies or complained at the sea. Those people are dead, this is a wholly new generation to whom Moshe seems to be speaking as if they were their parents.
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